# Organic chemistry – 14.3 Bonding: structural formulas

Bonding

Structural formulas

Outline

Structural formulas

Outline

Saturation

Degree of saturation

Degree of saturation

Bonding

Structural formulas

Saturation

Outline

Structural formulas

Saturation

Outline

Term: saturated

Term: unsaturated

Concept: saturated compound

Concept: unsaturated compound

Term: unsaturated

Concept: saturated compound

Concept: unsaturated compound

Bonding

Structural formulas

Saturation

Term: saturated

Structural formulas

Saturation

Term: saturated

– Contains no pi bonds

– no rings

– no rings

Bonding

Structural formulas

Saturation

Term: unsaturated

Structural formulas

Saturation

Term: unsaturated

– contains at least one pi bond or a ring

Bonding

Structural formulas

Saturation

n

Structural formulas

Saturation

n

carbon

Bonding

Structural formulas

Saturation

Concept: saturated compound

Structural formulas

Saturation

Concept: saturated compound

A saturated compound with n carbon atoms has exactly 2n+2 hydrogen atoms

Bonding

Structural formulas

Saturation

Concept: unsaturated compound

Structural formulas

Saturation

Concept: unsaturated compound

A unsaturated compound with n carbon atoms has fewer than 2n+2 hydrogens.

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Outline

Structural formulas

Degree of unsaturation of simple organic molecules

Outline

d

Formula of degree of unsaturation

Formula of degree of unsaturation: n

Formula of degree of unsaturation: x

Formula of degree of unsaturation: x (other atoms)

Degree of unsaturation and hybrid bonds

Examples

Formula of degree of unsaturation

Formula of degree of unsaturation: n

Formula of degree of unsaturation: x

Formula of degree of unsaturation: x (other atoms)

Degree of unsaturation and hybrid bonds

Examples

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

d

Structural formulas

Degree of unsaturation of simple organic molecules

d

degree of unsaturation

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation

((2n+2)-x)/2

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation: n

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation: n

carbons

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation: x

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation: x

hydrogens

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation: x (other atoms)

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation: x (other atoms)

x represents the number of hydrogens and any monovalent atoms

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation: x (monovalent atoms)

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation: x (monovalent atoms)

Such as halogens:

F

Cl

Br

I

F

Cl

Br

I

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation: x (oxygen)

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation: x (oxygen)

Since the number of oxygens has no effect, it is ignored.

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation: x (nitrogen)

Structural formulas

Degree of unsaturation of simple organic molecules

Formula of degree of unsaturation: x (nitrogen)

for nitrogen-containing compounds, replacing each N by 1 C and 1 H when using this formula.

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Degree of unsaturation and hybrid bonds

Indication: one degree of unsaturation

Structural formulas

Degree of unsaturation of simple organic molecules

Degree of unsaturation and hybrid bonds

Indication: one degree of unsaturation

One degree of unsaturation:

presence of

– one pi bond or

-one ring

presence of

– one pi bond or

-one ring

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Degree of unsaturation and hybrid bonds

Indication: two degrees of unsaturation

Structural formulas

Degree of unsaturation of simple organic molecules

Degree of unsaturation and hybrid bonds

Indication: two degrees of unsaturation

Possibilites:

– two bi bonds (two separate double bonds or one triple bond), or

– one pi bond and one ring or

– two rings

and so on.

– two bi bonds (two separate double bonds or one triple bond), or

– one pi bond and one ring or

– two rings

and so on.

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Degree of unsaturation and hybrid bonds

Example: one degree of unsaturation

4-Chlorobutene (C4H7Cl)

Structural formulas

Degree of unsaturation of simple organic molecules

Degree of unsaturation and hybrid bonds

Example: one degree of unsaturation

4-Chlorobutene (C4H7Cl)

– 4 carbon, 7 hydrogen

– Number of hydrogen is different.

– each halogen atom (F, Cl, B, I) or other monovalent atom “replaces” one hydrogen atom, so

d= ((2.4+2)-(7-1))/2=1

– Number of hydrogen is different.

– each halogen atom (F, Cl, B, I) or other monovalent atom “replaces” one hydrogen atom, so

d= ((2.4+2)-(7-1))/2=1

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Formula

divalent atom

Structural formulas

Degree of unsaturation of simple organic molecules

Formula

divalent atom

replace one carbon and two hydrogen atoms

Bonding

Structural formulas

Degree of unsaturation of simple organic molecules

Degree of unsaturation and hybrid bonds

example: one degree of unsaturation

Methoxyethene (C3H6O)

Structural formulas

Degree of unsaturation of simple organic molecules

Degree of unsaturation and hybrid bonds

example: one degree of unsaturation

Methoxyethene (C3H6O)

– 3 carbons, 6 hydrogen

– each oxygen (or other divalent atom) replaces one carbon and two hydrogen atoms.

– CH2 groups are sometimes referred to as methylene groups

so d= ((2(3+1)+2)-(6+2))/2=1

– each oxygen (or other divalent atom) replaces one carbon and two hydrogen atoms.

– CH2 groups are sometimes referred to as methylene groups

so d= ((2(3+1)+2)-(6+2))/2=1

– Since a divalent atom can take the place of a methylene group, it does not affect the degree of unsaturation, and can be ignored.

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